57056-81-2Relevant academic research and scientific papers
Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines
Yi, Jaeeun,Kim, Hyun Tae,Jaladi, Ashok Kumar,An, Duk Keun
supporting information, p. 129 - 132 (2021/11/17)
Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.
Bis(trialkylsilyl) peroxides as alkylating agents in the copper-catalyzed selective mono-: N -alkylation of primary amides
Sakamoto, Ryu,Sakurai, Shunya,Maruoka, Keiji
supporting information, p. 6484 - 6487 (2017/07/10)
The copper-catalyzed selective mono-N-alkylation of primary amides with bis(trialkylsilyl) peroxides as alkylating agents was reported. The results of a mechanistic study suggest that this reaction should proceed via a free radical process that includes the generation of alkyl radicals from bis(trialkylsilyl) peroxides.
Directed Lithiation of Tertiary β-Amino Benzamides
Comins, Daniel L.,Brown, Jack D.
, p. 3566 - 3572 (2007/10/02)
The directed ortho-lithiation-alkylation of several tertiary β-amino benzamides was studied.The ortho-substituted β-amino benzamides were hydrolyzed directly with 6 N hydrochloric acid, or by a three-step, one-pot reaction involving methylation, elimination, and treatment with aqueous acid. o-Toluic acid, 2-n-butylbenzoic acid, 2-methoxy-6-methylbenzoic aicd, and 4-methoxy-2-methylbenzoic acid were prepared by using this ortho-metalation-hydrolysis methodology.Ortho-lithiation and reaction with benzaldehyde or dimethylformamide followed by hydrolysis with aqueous acid gave lactones in good yield.Methanolysis of N-(4-methoxy-2-methyl benzoyl)-N'-methylpiperizine with sulfuric acid/methanol gave methyl 4-methoxy-2-methylbenzoate in 71percent yield.The conversion of tertiary benzamides into ketones and aldehydes was examined.Treatment of certain tertiary benzamides with alkyllithium reagents gave ketones, while reaction with a modified aluminum hydride reagent gave aldehydes
